2-benzyl-7-methoxybenzo[d][1,2]selenazol-3(2H)-one | 1347749-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-benzyl-7-methoxybenzo[d][1,2]selenazol-3(2H)-one
• 英文别名: 2-Benzyl-7-methoxy-1,2-benzoselenazol-3-one；2-benzyl-7-methoxy-1,2-benzoselenazol-3-one
• CAS: 1347749-16-9
• 化学式: C₁₅H₁₃NO₂Se
• 分子量: 318.234
• InChiKey: CADWFDPXXAOHGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-chloro-3-methoxy-N-benzylbenzamide 在 selenium 、 copper(l) iodide 、 1,10-菲罗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以67%的产率得到2-benzyl-7-methoxybenzo[d][1,2]selenazol-3(2H)-one
  参考文献：
  名称：

  Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones

  摘要：

  Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.141

文献信息

• Isoselenazolones as Catalysts for the Activation of Bromine: Bromolactonization of Alkenoic Acids and Oxidation of Alcohols
  作者：Shah Jaimin Balkrishna、Ch Durga Prasad、Piyush Panini、Michael R. Detty、Deepak Chopra、Sangit Kumar

  DOI：10.1021/jo301486c

  日期：2012.11.2

  selenium powder. The catalytic activity of the various isoselenazolones was studied in the bromolactonization of pent-4-enoic acid. Isoselenazolone 9 was studied as a catalyst in several reactions: the bromolactonization of a series of alkenoic acids with bromine or N-bromosuccinimide (NBS) in the presence of potassium carbonate as base, the bromoesterification of a series of alkenes using NBS and a variety

  异硒烯酮是通过2-卤代苯甲酰胺与硒粉之间的铜催化Se-N键形成反应合成的。研究了异戊烯酮在戊-4-烯酸的溴化中的催化活性。研究了异壬烯酮9在以下反应中的催化剂：在碳酸钾为碱的情况下，用溴或N-溴丁二酰亚胺（NBS）溴化一系列链烯酸，使用NBS以及一系列其他方法对一系列烯烃进行溴酯化羧酸，以及使用溴作为氧化剂将仲醇氧化为酮。77揭示了异硒唑啉酮催化的溴化反应的机理细节Se NMR光谱和ES-MS研究。将溴氧化添加至异硒唑啉酮可得到二溴异硒唑酮（IV），这可能是反应条件下溴的活化的原因。从空间位阻效应Ñ苯基乙基对isoselenazolone和的酰胺基团的吸电子的isoselenazolone的苯并稠合的环上的取代基氟出现增强isoselenazolone的稳定性作为用于溴化反应的催化剂。
• Synthesis of Benzoisoselenazolones via Rh(III)‐Catalyzed Direct Annulative Selenation by Using Elemental Selenium
  作者：Qing‐Feng Xu‐Xu、Yuji Nishii、Yuta Uetake、Hidehiro Sakurai、Masahiro Miura

  DOI：10.1002/chem.202103485

  日期：2021.12.20

  A Rh(III)-catalyzed direct selenium annulation by using stable and tractable elemental selenium is developed. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions to give isoselenazolone derivatives. An unprecedented selenation mechanism involving an electrophilic Se(IV) species as the reactive selenium donor is proposed based on the designed

  使用稳定且易处理的元素硒开发了Rh(III) 催化的直接硒环化。在温和的反应条件下，一系列苯甲酰胺和丙烯酰胺与硒成功偶联，得到异硒唑酮衍生物。基于设计的控制实验、X 射线吸收光谱和计算研究，提出了一种前所未有的硒化机制，涉及亲电子 Se(IV) 物种作为反应性硒供体。
• Copper catalyzed/mediated synthetic methodology for ebselen and related isoselenazolones
  作者：Shah Jaimin Balkrishna、Bhagat Singh Bhakuni、Sangit Kumar

  DOI：10.1016/j.tet.2011.09.141

  日期：2011.12

  Scope of the copper catalyzed/mediated selenium-nitrogen coupling reaction has been studied for the synthesis of isoselenazolones. It is noticed that the 2-chloro, 2-bromo-, and 2-iodo-aryl amides substrates can be exploited in the selenium-nitrogen coupling reaction by employing 25-100 mol % of CuI/1,10-phenanthroline (L) and potassium carbonate as a base in DMF. Furthermore, electron rich 2-chloro-arylamides also underwent selenium-nitrogen coupling reaction to give biologically important selenium-nitrogen heterocycles. Also, copper-catalyzed selenium-nitrogen coupling reaction has been meticulously applied for the synthesis of diaryl diselenides having methoxy, amine, and amide functionality from respective aryl iodides in the presence of stoichiometric amount of succinimide as an external Se-N coupling partner. (C) 2011 Elsevier Ltd. All rights reserved.